| |
 |
Medical devices and applications of polyhydroxyalkanoate polymers |
| 7553923 |
Medical devices and applications of polyhydroxyalkanoate polymers
|
|
| Patent Drawings: | |
| Inventor: |
Williams, et al. |
| Date Issued: |
June 30, 2009 |
| Application: |
11/925,635 |
| Filed: |
October 26, 2007 |
| Inventors: |
Williams; Simon F. (Sherborn, MA)
Martin; David P. (Arlington, MA)
Skraly; Frank A. (Watertown, MA)
|
| Assignee: |
Metabolix, Inc. (Cambridge, MA) |
| Primary Examiner: |
Boykin; Terressa M |
| Assistant Examiner: |
|
| Attorney Or Agent: |
Pabst Patent Group LLP |
| U.S. Class: |
528/354; 264/176.1; 264/211; 424/423; 435/135; 523/124; 528/272 |
| Field Of Search: |
264/176.1; 264/211; 424/423; 523/124; 528/354; 528/272; 435/135 |
| International Class: |
C08G 63/08 |
| U.S Patent Documents: |
|
| Foreign Patent Documents: |
2307637; 2259098; 2298421; 39 37 649; 0 258 781; 0 344 704; 0 349 505; 0 423 484; 0 429 403; 0 432 443; 0 452 111; 0 507 554; 0 601 885; 0 628 586; 0 754 467; 1130043; 1266984; 2166354; 62-209144; 03-187386; 04-292619; 04-326932; 4-326932; 5-023189; 5-194141; 06-264306; 06-336523; 7-275344; 07-275344; 08-089264; 09-098793; 09-507091; WO 92/18164; WO 93/05824; WO 93/20134; WO 94/02184; WO 94/06886; WO 95/03356; WO 95/17216; WO 95/20614; WO 95/20615; WO 95/20621; WO 95/23250; WO 95/33874; WO 96/00263; WO 96/08535; WO 96/18420; WO 96/21427; WO 96/40304; WO 97/04036; WO 97/07153; WO 97/15681; WO 97/30042; WO 98/04292; WO 98/39453; WO 98/48028; WO 98/51812; WO 99/11196; WO 99/14313; WO 99/32536; WO 99/35192; WO 00/51662; WO 00/56376; WO 01/10421; WO 01/15671; WO 01/19361; WO 2004/101002 |
| Other References: |
Abate, et al., "Separation and structural characterizations of cyclic and open chain oligomers produced in the partial pyrolysis of microbialpoly(hydroxyutyrates)", Macromolecules, 28(23):7911-1916 (1995). cited by other.
Addolorato, et al., "Maintaining abstinence from alcohol with gamma-hydroxybutyric acid", The Lancet, 351:38 (1998). cited by other.
Agostini, et al., "Synthesis and Characterization of Poly-.beta.-Hydroxybutyrate. I. Synthesis of Crystalline DL Poly-.beta.-Hydroxybutyrate from DL-.beta.-Butyrolactone," Polym. Sci., Part A-1 9:2775-87 (1971). cited by other.
Akhtar, "Physiomechanical Properties of bacterial P(HB-HV) Polyesters and Their Uses in drug Delivery," The British Library Document Supply Centre, UMI, (1990). cited by other.
Anderson, et al., "Occurrence, Metabolism, metabolic Role, and Industrial Uses of bacterial Polyhydroxyalkanoates," Microbiological Reviews pp. 450-472 (1990). cited by other.
Andriamampandry, et al., "Cloning of a rat brain succinic semialdehyde reductase involved in the synthesis of the neuromodulator .gamma.-hydroxybutyrate", Biochem. J., 334:43-50 (1998). cited by other.
Bailey, "Free radical ring-opening polymerization," J. Polym. Preprints 25:210-11 (1984). cited by other.
Bailey, et al., "Synthesis of Poly-.epsilon.-caprolactone via a free radical mechanism. Free radical ring-opening polymerization of 2-methylene-1,3-dioxepane", J. Polym. Sci. Polym. Chem., 20:3021-30 (1982). cited by other.
Bandiera, et al., "Effect of sodium sulfonate groups on the ionic conductivity of a copolyester of thiodipropionic acid", Eur. Pol. J., 33:1679-1683 (1997). cited by other.
Behrend, "PHB as a bioresorbable material for intravascular stents," American J. Cardiol. p. 45, TCT Abstracts (Oct. 1998). cited by other.
Berde, et al., "Sustained release of dibucaine from a biodegradable polymer matrix: A potential method for prolooged neural blockade", Abstracts of Scientific Papers, 1990 Annual Meeting, Ameri. Soc. Anesthesiologists, 73(3A):A776 Sep. (1990). citedby other.
Berger, et al., "PHB recovery by hypochlorite digestion of non-PHB biomass", Biotechnonology Techniques, 3(4):227-232 (1989). cited by other.
Blight, "Miracles and molecules--progress in spinal cord repair.," Nat. Neurosci 5:1051-4 (2002). cited by other.
Boeree, et al., "Development of a degradable composite for orthopaedic use: mechanical evaluation of an hydroxyapatite-polyhydroxybutyrate composite material", Biomaterials, 14(10):793-6 (1993). cited by other.
Brandl, et al., "Pseudomonas oleovorans as a source of poly(b-hydroxyalkanoates for potential applications as biodegradable polyesters", Appl. Environ. Microbiol., 54:1977-1982 (1988). cited by other.
Braunegg, et al., "Polyhydroxyalkanoates, biopolyesters from renewable resources: physiological and engineering aspects," J. Biotech. 65: 127-161 (1998). cited by other.
Breuer, et al., "Tissue Engineering Lamb Heart Valve Leaflets," Biotechnology & Bioengineering 50:562-67 (1996). cited by other.
Bruhn & Muller, "Preparation and characterization of spray-dried Poly(DL-Lactide) Micro Spheres," Proceed. Intern. Symp. Control. Rel. Bioact. Mater. 18:668-69 (1991). cited by other.
Byrom, "Miscellaneous Biomaterials," in Biomaterials (D. Byrom, ed.) pp. 333-359 MacMillan Publishers: London, 1991. cited by other.
Campbell & Bailey, "Mechanical properties of suture materials in vitro and after in vivo implantation in horses," Vet. Surg. 21(5):355-61 (1992). cited by other.
Chu, et al., Wound Closure Biomaterials and Devices CRC Press:Boca Raton, 1996. cited by other.
Colombo, et al., "Involvement of GABA(A) and GABA(B) receptors in the mediation of discriminative stimulus effects of gamma-hydroxybutyric acid", Physiology & Behavior, 64:293-302 (1998). cited by other.
Conti, et al., "Use of polylactic acid for the preparation of microparticulate drug delivery systems," J. Microencapsulation 9:153-166 (1992). cited by other.
Cookson, "It grows on trees," Financial Times p. 6 (Aug. 12, 1992). cited by other.
Cuebas, et al., "Mitochondrial metabolism of 3-mercaptopropionic acid. Chemical synthesis of 3-mercaptopropionyl coenzyme A and some of its S-acyl derivatives", J. Biol. Chem., 260:7330-7336 (1985). cited by other.
Damien & Parsons, "Bone graft and bone graft substitutes: a review of current technology and applications," J. Appl. Biomater. 2(3):187-208 (1991). cited by other.
Dayton, et al., "Use of an absorbable mesh to repair contaminated abdominal-wall defects", Arch Surg. , 121:954-960 (1986). cited by other.
De Groot, "Meniscal tissue regeneration in porous 50/50 copoly(L-lactide/epsilon-caprolactone) implants," Biomaterials 18(8):613-22 (1997). cited by other.
De Koning, et al., "A biodegradable rubber by crosslinking poly(hydroxyalkanoate) from Pseudomonas oleovorans", Polymer, 35:2090-97 (1994). cited by other.
De Smet, et al., "Characterization of Intracellular inclusions formed by Pseudomonas oleovorans during growth on octane," J. Bacteriol. 154:870-78 (1983). cited by other.
Domb, et al., Handbook of Biodegradable Polymers (Harwood Academic Publishers:Amsterdam, The Netherlands, 1997). cited by other.
Dubois, et al., "Macromolecular Engineering of Polylactones and Polylactides. 12. Study of the Depolymerization Reactions of Poly (.epsilon.-caprolactone) with Functional Aluminum Alkoxide End Groups," Macromolecules 26:4407-12 (1993). cited byother.
Duvernoy, et al. "A biodegradable patch used as a pericardial substitute after cardiac surgery: 6- and 24-month evaluation with CT," Thorac. Cardiovasc. Surg. 43(5):271-74 (1995). cited by other.
Encyclopedic Handbook of Biomaterials and Bioengineering, Part A: Materials, vol. 1 eds. Wise, et al.; Marcel Dekker, Inc., New York, 1995. cited by other.
Entholzner, et al., "EEG changes during sedation with gamma-hydroxybutyric acid", Anaesthesist, 44:345-350 (1995). cited by other.
Fraser, et al., "Controlled release of a GnRH agonist from a polyhydroxybutyric acid implant-reversible suppression of the menstrual cycle in the macaque," Acta Endocrinol 121:841-848 (1989). cited by other.
Freed, et al., "Biodegradable polymer scaffolds for tissue engineering", Biotechnology, 12:689-693 (1994). cited by other.
Fuchtenbusch, et al., "Biosynthesis of novel copolyesters containing 3-hydroxypivalic acid by Rhodoccus ruber NCIMB 40126 and related bacteria", FEMS Microbiol. Lett., 159:85-92 (1998). cited by other.
Fukuzaki, et al., "Direct copolymerization of L-lactic acid with .gamma.-butyrolactone in the absence of catalysts," Die Madromoleculare Chemie 190:1553-59 (1989). cited by other.
Gabbay, et al., "New outlook on pericardial substitution after open heart operations", Ann. Thorac. Surg., 48(6):803-12 (1989). cited by other.
Gagnon, et al., "A thermoplastic elastomer produced by the bacterium Pseudomonas oleovarans," Rubber World 207:32-38 (1992). cited by other.
Gagnon, et al., "Chemical modification of bacterial elastomers: 1. Peroxide crosslinking," Polymer 35:4358-67 (1994). cited by other.
Gagnon, et al., "Chemical modification of bacterial elastomers: 2. Sulfur vulvanization", Polymer, 35:4368-75 (1994). cited by other.
Gerngross & Martin, "Enzyme-catalyzed synthesis of poly[(R)-(-)-3-hydroxybutyrate]: formation of macroscopic granules in vitro," Proc. Natl. Acad. Sci. USA 92:6279-83 (1995). cited by other.
Gerra, et al., "Flumazenil effects on growth hormone response to gamma-hydroxybutyric acid", International Clinical Psychopharmacology, 9:211-215 (1994). cited by other.
Griebel, et al., "Metabolism of poly-beta-hydroxybutyrate. I. Purification, composition, and properties of native poly-beta-hydroxybutyrate granules from Bacillus megaterium", Biochemistry, 7:3676-3681 (1968). cited by other.
Gross, et al., "Polymerization of .beta.-Monosubstituted-.beta.-propiolactones Using Trialkylaluminum-Water Catalytic Systems and Polymer Characterization," Macromolecules 21:2657-68 (1988). cited by other.
Gugala, et al., Regeneration of segmental diaphyseal defects in sheep tibiae using resorbable polymeric membranes: a preliminary study, J. Orthop. Trauma. 13(3):187-95 (1999). cited by other.
Gursel, et al., "In vivo application of biodegradable controlled antibiotic release systems for the treatment of implant-related osteomyelitis," Biomaterials 22: 73-80 (2001). cited by other.
Hadlock, et al., "Ocular cell monolayers cultured on biodegradable substrates," Tissue Eng. 5(3):187-96 (1999). cited by other.
Hazari, et al., "A new resorbable wrap-around implant as an alternative nerve repair technique", J. Hand Surgery, 24(3): 291-295 (1999). cited by other.
Hazari, et al., "A resorbable nerve conduit as an alternative to nerve autograft in nerve gap repair", Br J Plast Surg., 52(8):653-7 (1999). cited by other.
Hein, et al., "Biosynthesis of poly(4-hydroxybutyric acid) by recombinant strains of Escherichia coli," FEMS Microbiol. Lett. 153:411-18 (1997). cited by other.
Heydorn, et al., "A new look at pericardial substitutes," J. Thorac. Cardiovasc. Surg. 94:291-96 (1987). cited by other.
Hocking & Marchessault, "Syndiotactic poly[(R,S)-.beta.-hydroxybutyrate] isolated from methyaluminoxane-catalyzed polymerization," Polym. Bull. 30:163-70 (1993). cited by other.
Hocking & Marchessault, "Biopolyesters" in Chemistry and Technology of Biodegradable Polymers, (G.J.L. Griffin, ed.), pp. 48-96, Chapman and Hall: London, 1994. cited by other.
Hoke, "Mechanisms of Disease: what factors limit the success of peripheral nerve regeneration in humans?" Nat. Clin. Pract. Neurol. 448-454 (2006). cited by other.
Holmes, "Biologically Produced (R)-3-hydroxyalkanoate Polymers and Copolymers," in Developments in Crystalline Polymers (Bassett, ed.), pp. 1-65, Elsevier: London, 1988. cited by other.
Holmes, et al., "Applications of PHB--a microbially produced biodegradable thermoplastic," Phys Technol 16:32-36 (1985). cited by other.
Hori, et al., "Chemical synthesis of high molecular weight poly(3-hydroxybutyrate-co-4-hydroxybutyrate)," Polymer 36:4703-05 (1996). cited by other.
Hori, et al., "Ring-Opening Copolymerization of Optically Active .beta.-Butyrolactone with Several Lactones Catalyzed by Distannoxane Complexes: Synthesis of New Biodegradable Polyesters," Macromolecules 26:4388-90 (1993). cited by other.
Hori, et al., "Ring-Opening Polymerization of Optically Active .beta.-Butyrolactone Using Distannoxane Catalysts: Synthesis of High Molecular Wright Poly(3-hydroxybutyrate)," Macromolecules 26:5533-34 (1993). cited by other.
Horowitz, et al., "Novel Thermal Route to an Amorphous, Film-Forming Polymer Latex", Macromolecules, 32:3347-3352 (1999). cited by other.
Horsch, "Inheritance of Functional Foreign Genes in Plants" Science, 223: 496-498 (1984). cited by other.
Huijberts, et al., "Pseudomonas putida KT2442 cultivated on glucose accumulates poly(3-hydroxyalkanoates) consisting of saturated and unsaturated monomers", Appl Environ Microbiol., 58(2):536-44 (1992). cited by other.
Hutmacher, et al., " A review of material properties of biodegradable and bioresorbable polymers and devices for GTR and GBR applications," Int. J. Oral Maxillofac. Implants 11(5):667-78 (1996). cited by other.
Kameyama, et al., "Novel sequence-ordered polymers by transformation of polymer backbone: Quantitative and regioselective insertion of Thiranes into poly(S-aryl thioester)", Macromol., 32:1407-1412 (1999). cited by other.
Kassab, et al., "Embolization with polyhydroxybutyrate (PHB) microspheres: In vivo studies", J. Bioact. Compat. Polym., 14:291-303 (1999). cited by other.
Kaufman and Nelson, "An overview of gamma-hydroxybutyrate catabolism: the role of the cytosolic NADP(+)-dependent oxidoreductase EC 1.1.1.19 and of a mitochondrial hydroxyacid-oxoacid transhydrogenase in the initial, rate-limiting step in thispathway", Neurochemical Research, 16:965-974 (1991). cited by other.
Keeler, "Don't Let Food Go To Waste--Make Plastic Out of It," R&D Magazine pp. 52-57 (1991). cited by other.
Keeler, "Plastics Grown in Bacteria Inch Toward the Market," R&D Magazine pp. 46-52 (1991). cited by other.
Kemnitzer, et al., "Preparation of predominantly Syndiotactic Poly(.beta.-hydroxybutyrate) by the Tributylin Methoxide Catalyzed Ring-Opening Polymerization of racemic .beta.-Butyrolactone," Macromolecules 26:1221-29 (1993). cited by other.
Kim and Mooney, "Engineering smooth muscle tissue with a predefined structure", J. Biomed. Mat. Res., 41(2):322-332 (1998). cited by other.
Kishida, et al., "Formulation-assisted biodegradable polymer matrices," Chemical and Pharmaceutical Bulletin 37:1954-56 (1989). cited by other.
Kleinschmidt, et al., "Continuous sedation during spinal anaesthesia: gamma-hydroxybutyrate vs. propofol", European Journal of Anaesthesiology, 16:23-30 (1999). cited by other.
Kleinschmidt, et al., "Total intravenous anaesthesia using propofol, gamma-hydroxybutyrate or midazolam in combination with sufentanil for patients undergoing coronary artery bypass surgery", European Journal of Anesthesiology, 14:590-599 (1997).cited by other.
Klinge, et al., "Functional assessment and tissue response of short- and long-term absorbable surgical meshes", Biomaterials, 22:1415-1424 (2001). cited by other.
Koosha, "Preparation and characterization of biodegradable polymeric drug carriers," Ph.D. Dissertation, 1989, Univ. Nottingham, UK., Diss. Abstr. Int. B 51:1206 (1990). cited by other.
Koosha, et al., "Polyhydroxybutyrate as a drug carrier," Crit. Rev. Ther. Drug Carrier Syst. 6(2):117-30 (1989). cited by other.
Korkusuz, et al., In vivo response to biodegradable controlled antibiotic release systems, J. Biomed. Mater. Res. 55: 217-228 (2001). cited by other.
Korsatko, et al., "The influence of the molecular weight of poly-D-(-)-3-hydroxybutyric acid on its use as a retard matrix for sustained drug release," 8.sup.th Europ. Congress of Biopharmaceutics and Pharmokinetics 1:234-242 (1987). cited by other.
Korte & Gelt, "Hochdruckreaktionen. II. Die Polymerisation Von .gamma. butyrolacton und .delta.-valerolactam bei hohen drucken," Polymer Lett. 4:685-89 (1966). cited by other.
Kusaka, et al., "Microbial synthesis and Physical Properties of ultra-high-molecular-weight poly[(R)-3-hydroxybutyrate]," Pure Appl. Chem. A35:319-35 (1998). cited by other.
Lafferty, et al., "Microbial Production of Poly-b-hydroxybutyric acid" in Biotechnology (Rehm & Reed, Eds.), pp. 135-176, Verlagsgesellschaft:Weinheim, 1988. cited by other.
Lafferty, et al., "Microbial Production of Poly-b-hydroxybutyric acid" in Biotechnology (H.J. Rehm and G. Reed, eds.), Verlagsgesellschaft, Weinheim, vol. 66, pp. 135-176 (1988). cited by other.
Lamba, et al., "Degradation of polyurethanes", in Polyurethanes in Biomedical Applications (CRC Press:Boca Raton, Florida, 1998). cited by other.
Lamba, et al., Polyurethanes in Biomedical Applications (CRC Press:Boca Raton, Florida, 1998). cited by other.
Lanza, et al., Principles of Tissue Engineering (Academic Press:Austin, 1997). cited by other.
Le Borgne and Spassky, "Stereoelective polymerization of .beta.-butyrolactone", Polymer, 30:2312-19 (1989). cited by other.
Lebedev and Yevstropov, "Thermoplastic properties of polylactones", Makromol. Chem., 185:1235-1253 (1984). cited by other.
Lee, et al., "Copolymerization of -butyrolactone and .beta.-butyrolactone", Macromol. Chem. Phys., 198:1109-20 (1997). cited by other.
Lemoigne & Roukhelman, "Fermetation .beta.-Hydroxybutyrique Caracterisation et Evolution Des Produits de Deshydration et de Polymerisation de L'acide .beta.-Dehydroxybutyrique," Annales des fermentations, 5:527-36 (1925). cited by other.
Ljungberg, et al. "Neuronal survival using a resorbable synthetic conduit as an alternative to primary nerve repair", Microsurgery, 19(6):259-264 (1999). cited by other.
Lloyd, et al., "Transformation of Arabidopsis thalania with Agrobacterium tumefaciens," Science 234: 464-66 (1986). cited by other.
Lutke-Eversloh et al., "Identification of a new class of biopolymer: Bacterial synthesis of a sulfur-containing polymer with thioester linkages", Microbiology, 147(1): 11-19 (2001). cited by other.
Lutke-Eversloh et al., "List of submitted abstracts", The 8.sup.th International Symposium on Biological Polyesters, (2000). cited by other.
Madison & Huisman, "Metabolic engineering of poly(3-hydroxyalkanoates): from DNA to plastic," Microbiol. Molec. Biol. Rev. 63:21-53 (1999). cited by other.
Malm, et al., "A new biodegradable patch for closure of atrial septal defect. An experimental study," Scand. J. Thorac. Cardiovasc. Surg. 26(1):9-14 (1992). cited by other.
Malm, et al., "Enlargement of the right ventricular outflow tract and the pulmonary artery with a new biodegradable patch in transannular position," Eur. Surg. Res. 26(5):298-308 (1994). cited by other.
Malm, et al., "Prevention of postoperative pericardial adhesions by closure of the pericardium with absorbable polymer patches. An experimental study," J. Thorac. Cardiovasc. Surg. 104(3):600-07 (1992). cited by other.
Martin and Williams, "Medical application of poly-4-hydroxybutyrate: A strong flexible absorbable biomaterial", Biochem. Eng. J., 16:97-105 (2003). cited by other.
Mathiowitz & Langer, "Polyanhydride microspheres as drug delivery systems" in Microcapsules Nanopart. Med. Pharm. (Donbrow, ed.), pp. 99-123 (CRC:Boca Raton, Florida, 1992). cited by other.
Maysinger, et al., "Microencapsulation and the Grafting of Genetically Transformed Cells as Therapeutic Strategies to rescue Degenerating Neurons of the CNS,"Reviews in the Neurosciences, 6:15-33 (1995). cited by other.
McMillin, et al., "Elastomers for Biomedical Applications," Rubber Chemistry and Technology 67:417-446 (1994). cited by other.
McWilliams, "Plastics as High as an Elephant's Eye?" Business Week, pp. 110-111 (1991). cited by other.
Modelli, et al., "Kinetics of aerobic polymer degradation in soil by means of the ASTM D 5988-96 standard method," J Environ Polym Degr 7:109-116 (1999). cited by other.
Muh, et al., "PHA synthase from chromatium vinosum: cysteine 149 is Involved in covalent catalysis", Bioche., 38:826-837 (1999). cited by other.
Muller, et al., "Poly(hydroxyalkanoates): A Fifth Class of Physiologically Important Organic Biopolymers," Angew. Chem. Int. Ed. Engl. 32: 477-502 (1993). cited by other.
Nakamura et al., "Biosynthesis and characteristics of bacterial poly(3-hydroxybutyrate-co-3-hydroxypropionate)", Macromol. Rep., A28, 15-24 (1991). cited by other.
Nakamura, et al., "Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate)," Macromol. 25:4237-41 (1992). cited by other.
Nelson, et al., "The extraneural distribution of gamma-hydroxybutyrate", J. Neurochem., 37:1345-1348 (1981). cited by other.
Niklason, et al., "Functional arteries grown in vitro," Science 284(5413):489-93 (1999). cited by other.
Nobes, et al., "Polyhydroxyalkanoates: Materials for delivery systems," Drug Del. 5:167-77 (1998). cited by other.
Ogawa, et al., "A New Technique to Efficiently Entrap Leuprolide Acetate into Microcapsules of Poly Lactic Acid or Copoly(Lactic/Glycolic) Acid," Chem. Pharm. Bull. 36:1095-103 (1988). cited by other.
Otera, et al., "Distannoxane as reverse micelle-type catalyst: novel solvent effect on reaction rate of transesterification," J. Org. Chem. 54:4013-14 (1989). cited by other.
Otera, et al., "Distannoxane-catalysed transesterification of 1,n-Dioldiacetates. Selective transformation of either of chemically equivalent functional groups," J. Chem. Soc. Chem. Commun. 1742-43 (1991). cited by other.
Otera, et al., "Novel distannoxane-catalyzed transesterification and a new entry to .alpha.,.beta.-unsaturated carboxylic acids," Tetrahedron Lett., 27:2383-86 (1986). cited by other.
Otera, et al., "Novel template effects of distannoxanne catalysts in highly efficient transesterification and esterification," J. Org. Chem. 56:5307-11 (1991). cited by other.
Pedros-Alio et al., "The influence of poly-.beta.-hydroxybutyrate accumulation on cell volume and buoyant density in Alcaligenes eutrophus", Arch. Microbiol. 143:178-184 (1985). cited by other.
Peoples, et al., "Poly-.beta.-hydroxybutyrate Biosynthesis in Alcaligenes eutrophus H16," J. Biol. Chem 264(26):15293-97 (1989). cited by other.
Peoples, et al., "Polyhydroxybutyrate (PHB): A Model System for Biopolymer Engineering: II," in Novel Biodegradable Microbial Polymers (Dawes, ed.) pp. 191-202, Kluwer Academic Publishers:Netherlands (1990). cited by other.
Perrin & English, "Polycaprolactone," in Handbook of Bioabsorbable Polymers (Domb, et al., eds.) pp. 63-77 (Harwood, Amsterdam, 1997). cited by other.
Pinto, "Hydrogen Peroxide as depyrogenation agent for medical devices components", Revista De Saude Publica, 29(1):75-79 (1995). cited by other.
Poirier, "Perspectives on the production of polyhydroxyalkanoates in plants," FEMS Microbiology Reviews 103:237-46 (1992). cited by other.
Poirier, et al., "Progress Toward Biologically Produced Biodegradable thermoplastics," Adv. Mater. 5(1):30-37 (1993). cited by other.
Pool, "In Search of the Plastic Potato," Science 245: 1187-89 (1989). cited by other.
Pouton & Akhtar, "Biosynthetic polyhydroxyalkanoates and their potential in drug delivery," Adv. Drug Delivery Rev. 18:133-62 (1996). cited by other.
Rehm and Steinbuchel, "Biochemical and genetic analysis of PHA synthases and other proteins required for PHA synthesis", Int. J. Biol. Macromol. 25:3-19 (1999). cited by other.
Renstad, et al.,. "The influence of processing induced differences in molecular structure on the biological and non-biological degradation of poly (3-hydroxybutyrate-co-3-hydroxyvalerate), P(3-HB-co-3-HV)," Polymer Degradation and Stability63:201-211 (1999). cited by other.
Reynolds, Martindale: The Extra Pharmacopeia, p. 1264, (Thirty First Edition, Royal Pharmaceutical Society, London, 1997). cited by other.
Rivard, et al., "Fibroblast seeding and culture in biodegradable porous substrates," J. Appl. Biomater. 6(1):65-68 (1995). cited by other.
Ropero-Miller & Goldberger, "Recreational drugs. Current trends in the 90s", Clinics in Laboratory Medicine, 18:727-746 (1998). cited by other.
Sabbagh, et al., "3-Mercaptopropionic acid, a potent inhibitor of fatty acid oxidation in rat heart mitochondria", J. Biol. Chem. 260:7337-7342 (1985). cited by other.
Saito, et al., "Microbial synthesis and properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in Comamonas acidovorans," Int. J. Biol. Macromol. 16(2):99-104 (1994). cited by other.
Scharf, et al., "Pharmacokinetics of gammahydroxybutyrate (GHB) in narcoleptic patients", Sleep 21:507-514 (1998). cited by other.
Schlegel, et al., "Ein submersverfahren zur kultur wasserstoffoxydierender bakterien: Wachstumsphysiologische untersuchungen", Arch. Mikrobiol. 38:209-222 (1961). cited by other.
Schmidt, et al "Neural tissue engineering: strategies for repair and regeneration," Annu. Rev. Biomed. Eng. 5:293-347 (2003). cited by other.
Schwartz & Goodman, Plastic Materials and Processes, (Van Nostrand Reinhold Company:New York, 1982). cited by other.
Sendelbeck & Girdis, "Disposition of a 14C-labeled bioerodible polyorthoester and its hydrolysis products, 4-hydroxybutyrate and cis,trans-1,4-bis(hydroxymethyl)cyclohexane, in rats", Drug Metabolism & Disposition 13:291-295 (1985). cited by other.
Shin'oka & Mayer, "New frontiers in tissue engineering: tissue engineered heart valves" in Synthetic Bioabsorbable Polymer Scaffolds (Atala & Mooney, eds.) pp. 187-198 Birkhauser Boston, 1997. cited by other.
Shinoka, et al., "Creation of viable pulmonary artery autografts through tissue engineering," J. Thorac. Cardiovasc. Surg. 115(3):536-46 (1998). cited by other.
Shinoka, et al., "Tissue engineering heart valves: valve leaflet replacement study in a lamb model" Ann. Thorac. Surg. 60(6 Suppl):S513-16 (1995). cited by other.
Sim, et al., "PHA synthase activity controls the molecular weight and polydispersity of polyhydroxybutyrate in vivo," Nat. Biotechnol. 15(1):63-67 (1997). cited by other.
Skrede et al., "Thia fatty acids, metabolism and metabolic effects" in Biochim Biophys Acta 1344:115-31 (1997). cited by other.
Snead, "The gamma-hydroxybutyrate model of absence seizures: correlation of regional brain levels of gamma-hydroxybutyric acid and gamma-butyrolactone with spike wave discharges", Neuropharmacology 30:161-167 (1991). cited by other.
Song, et al., "Production of poly(4-hydroxybutyric acid) by fed-batch cultures of recombinant strains of Escherichia coli", Biotechnol. Lett. 21:193-197 (1999). cited by other.
Speer & Warren, "Arthroscopic shoulder stabilization, A role for biodegradable materials," Clin. Orthop. (291):67-74 (1993). cited by other.
Stanton & Gagne, "The remarkable catalytic activity of alkali-metal alkoxide clusters in the ester interchange reaction," J. Am. Chem. Soc. 119:5075-76 (1997). cited by other.
Steinbuchel & Valentin, "Diversity of bacterial polyhydroxyalkanoic acids", FEMS Microbiol. Lett., 128:219-28 (1995). cited by other.
Steinbuchel & Wiese, "A Pseudomonas strain accumulating polyesters of 3-hydroxybutyric acid and medium-chain-length 3-hydroxyalkanoic acids," Appl. Microbiol. Biotechnol. 37:691-97 (1992). cited by other.
Steinbuchel and Valentin, "Diversity of bacterial polyhydroxyalkanoic acids", FEMS Microbiol. Lett., 128:219-28 (1995). cited by other.
Steinbuchel, "Molecular basis for biosynthesis and accumulation of polyhydroxyalkanoic acids in bacteria," FEMS Microbiol. Rev. 103:217-230 (1992). cited by other.
Steinbuchel, "Polyhydroxyalkanoic Acids," in Biomaterials (D. Byrom ed.), pp. 123-213, MacMillan Publishers: London, 1991. cited by other.
Takagi et al., "Biosynthesis of polyhydroxyalkanoate with a thiophenoxy side group obtained from Pseudomonas putida", Macromolecules, 32: 8315-8318 (1999). cited by other.
Talja, et al., "Bioabsorbable and biodegradable stents in urology," J. Endourol. 11(6):391-97 (1997). cited by other.
Tanahashi, et al., "Thermal Properties and Stereoregularity of Poly(3-hydroxybutyrate) Prepared from optically Active .beta.-Butyrolactone with a Zinc-Based Catalyst," Macromolecules 24:5732-33 (1991). cited by other.
Tanaka, et al., "Clinical application of 4-hydroxybutyrate sodium and 4-butyrolactone in neuropsychiatric patients", Folia Psychiatrica et Neurologica 20:9-17 (1966). cited by other.
Tanguay, et al., "Current status of biodegradable stents," Cardiol. Clin. 12(4):699-713 (1994). cited by other.
Tsuruta, et al., Biomedical Applications of Polymeric Materials (CRC Press, Boca Raton, Florida, 1993). cited by other.
Tunnicliff, "Sites of action of gamma-hydroxybutyrate (GHB)--a neuroactive drug with abuse potential", Clinical Toxicology, 35:581-590 (1997). cited by other.
Turesin, et al., "Biodegradable polyhydroxyalkanoate implants for osteomyelitis therapy: in vitro antibiotic release," J. Biomater. Sci. Polymer Edn. 12: 195-207 (2001). cited by other.
Turke, "Absorbable Biomaterial is suited for diverse applications" (Jun. 3, 2002). Retrieved on Dec. 17, 2004, from http://www.devicelink.com/mpmn/archive/01/10/009.html. cited by other.
Unverdorben, et al., "Polyhydroxybutyrate (PHB) Biodegradable Stent-Experience in the Rabbit," American J. Cardiol. p. 46, TCT Abstracts (Oct. 1998). cited by other.
Valentin, et al., "Identification of 5-hydroxyhexanoic acid, 4-hydroxyaheptanoic acid and 4-hydroxyoctanoic acid as new constitutents of bacterial polyhydroxyalkanoic acids," Appl. Microbiol. Biotechnol. 46:261-67 (1996). cited by other.
Valentin, et al., "Production of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in recombinant Escherichia coli grown on glucose," J. Biotechnol. 58:33-38 (1997). cited by other.
Valentin, et al., "Identification of 4-hydroxyhexanoic acid as a constituent of biosynthetic polyhydroxyalkanoic acids from bacteria," Appl. Microbiol. Biotechnol. 36:507-514 (1994). cited by other.
Valentin, et al., "Identification of 4-hydroxyhexanoic acid as a new constituent of biosynthetic polyhydroxyalkanoic acids from bacteria," Appl. Microbiol. Biotechnol. 40:710-16 (1994). cited by other.
Von Schroeder, et al., "The use of polyactic acid matrix and periosteal grafts for the reconstruction of rabbit knee articular defects," J. Biomed. Mater. Res. 25(3):329-39 (1991). cited by other.
Wallen & Rohwedder, "Poly-.beta.-hydroxyalakaonate from Activated Sludge," Environ. Sci. Technol. 8:576-79 (1974). cited by other.
Widmer & Mikos, "Fabrication of biodegradable polymer scaffolds for tissue engineering" in Frontiers in Tissue Engineering (Patrick, et al., Eds.) Ch. II.5, pp. 107-20 (Elsevier Science, New York, 1998). cited by other.
Williams & Peoples, "Biodegradable plastics from plants," CHEMTECH 26:38-44 (1996). cited by other.
Williams & Peoples, "Making plastics green," Chem. Br. 33:29-32 (1997). cited by other.
Williams, et al., "Application of PHAs in Medicine and Pharmacy", Polyesters III, 4:91-127 (2002). cited by other.
Williams, et al., "PHA applications: addressing the price performance issue. I. Tissue engineering," Int. J. Biol. Macromol. 25(1-3): 111-121 (1999). cited by other.
Wodzinska, et al., "Polyhydroxybutyrate synthase: Evidence for covalent catalysis", J. Am. Chem. Soc. 118:6319-6320 (1996). cited by other.
Wong & Mooney, "Synthesis and properties of bioabsorbable polymers used as synthetic matrices for tissue engineering," in Synthetic Bioabsorbable Polymer Scaffolds (Atala, et al., eds.) pp. 51-82 (Birkhauser: Boston, 1997). cited by other.
Worsey and Williams, "Metabolism of toluene and xylenes by Pseudomonas putida (arvilla) mt-2: evidence for a new function of the TOL plasmid" J Bacteriol 124:7-13 (1975). cited by other.
Xie, et al., "Ring-opening Polymerization of .beta.-Butyrolactone by Thermophilic Lipases," Macromolecules 30:6997-98 (1997). cited by other.
Yagmurlu, et al. "Sublactam cefoperazone polyhydroxybutyrate-co-hydroxyvalerate Local antibiotic delivery system: In Vivo Effectiveness and Biocompatibility in the treatment of Implant-Related Experimental Osteomyelitis," J. Biomed. Mater. Res.46(4):494-503 (1999). cited by other.
Yamada, et al., "Development of a dural substitute from synthetic bioabsorbable polymers," J. Neurosurg. 86(6):1012-17 (1997). cited by other.
Yiu, et al. "Glial inhibition of CNS axon regeneration," Nat. Rev. Neurosci. 7:617-627 (2006). cited by other.
Zund, et al., "The in vitro construction of a tissue engineered bioprosthetic heart valve," Eur. J. Cardiothorac. Surg. 11(3):493-97 (1997). cited by other.
Kassab, "Rifampicin carrying polyhydroxybutyrate microspheres as a potential chemoembolization agent", Journal of Biomaterials Science, Polymer Edition, 8(12):947-961 (1997). cited by other.
Valappil, et al., "Biomedical applications of polyhydroxyalkanoates, an overview of animal testing and in vivo responses", Expert Rev. Med. Devices, 3(6):853-868 (2006). cited by other. |
|
| Abstract: |
Devices formed of or including biocompatible polyhydroxyalkanoates are provided with controlled degradation rates, preferably less than one year under physiological conditions. Preferred devices include sutures, suture fasteners, meniscus repair devices, rivets, tacks, staples, screws (including interference screws), bone plates and bone plating systems, surgical mesh, repair patches, slings, cardiovascular patches, orthopedic pins (including bone filling augmentation material), adhesion barriers, stents, guided tissue repair/regeneration devices, articular cartilage repair devices, nerve guides, tendon repair devices, atrial septal defect repair devices, pericardial patches, bulking and filling agents, vein valves, bone marrow scaffolds, meniscus regeneration devices, ligament and tendon grafts, ocular cell implants, spinal fusion cages, skin substitutes, dural substitutes, bone graft substitutes, bone dowels, wound dressings, and hemostats. The polyhydroxyalkanoates can contain additives, be formed of mixtures of monomers or include pendant groups or modifications in their backbones, or can be chemically modified, all to alter the degradation rates. The polyhydroxyalkanoate compositions also provide favorable mechanical properties, biocompatibility, and degradation times within desirable time frames under physiological conditions. |
| Claim: |
We claim:
1. A stent graft comprising a biodegradable polyhydroxyalkanoate composition that has a degradation rate under physiological conditions, wherein the degradation rate is controlled byaddition of components to the polyhydroxyalkanoate composition, selection of the chemical composition of the polyhydroxyalkanoate, selection of the weight average molecular weight of the polyhydroxyalkanoate, selection of the processing conditions of thepolyhydroxyalkanoate, or selection of the form of the composition, wherein the polyhydroxyalkanoate polymer has a weight average molecular weight of between 10,000 and 10,000,000 daltons.
2. The stent graft of claim 1 wherein the stent graft is supported by a stent.
3. The stent graft of claim 2 wherein the stent is absorbable.
4. The stent graft of claim 1 wherein the stent comprises a polyhydroxyalkanoate.
5. The stent graft of claim 2 wherein the stent graft further comprises a drug, growth factor and/or other active agent.
6. The stent graft of claim 2 wherein the stent is self expanding or balloon-expandable.
7. The stent graft of claims 2 wherein part or all of the stent graft or stent degrades over time.
8. The stent graft of claim 1 wherein the stent graft is used to treat a diseased vessel.
9. The stent graft of claim 8 wherein the diseased vessel comprises an aneurysm or plaque deposit.
10. The stent graft of claim 8 wherein the stent graft delivers a drug, growth factor or other active agent when deployed. |
| Description: |
|
|
|
|
